The best downtowns in Massachusetts are found in its small towns. Why is that? Well, oftentimes, the heart of a state lies within its small towns, and that’s certainly the case for Massachusetts. With mainly privately owned shops, boutiques, cafes, bars, and restaurants, you’ll be hard-pressed to find a big box or corporate-run store in the downtown areas of the small towns in Massachusetts. Here are some of the cutest town squares in Massachusetts:

1. Concord
Concord, MA, USA
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A quintessential New England town filled with colonial history, Concord has quite a lot to see. Spend some time exploring Minute Man National Historic State Park, Louisa May Alcott's Orchard House, The Old Manse, and Walden Pond before heading downtown. On and around Main Street, you'll encounter plenty of charming restaurants and shops. It's a lovely place to spend an afternoon. Learn more about one of the best small towns in Massachusetts, and then pay it a visit.
2. Provincetown
Provincetown, MA, USA
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Whether you take a ferry from Boston or drive up the Cape, Provincetown's downtown Commercial Street is a must-visit in Massachusetts. Climb up Pilgrim Monument, an imposing structure that was built to commemorate the Pilgrims landing on Cape Cod, where you can get panoramic water and downtown views. Peruse the shops, head to the historic MacMillan Wharf, walk along the beach, visit a gallery, buy some salt water taffy...there's so much to see and do in Provincetown!
3. Rockport
Rockport, MA, USA
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Rockport is one of the most picturesque towns in the Bay State and is located a mere 40 miles from Boston. Its downtown area can be found along Main Street as well as Bearskin Neck, an art colony filled with galleries, shops, and restaurants. If you want to pick up a piece of locally-made art or jewelry, Bearskin Neck is the place to go. So with one of the best downtown shopping districts in Massachusetts, you won't want to pass this town by.

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4. Falmouth
Falmouth, MA, USA
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Main Street in Falmouth covers a long stretch where you will find a bookstore, clothing boutiques, gift and home decor shops, ice cream shops, and several bars and restaurants. If you want to spend the night, you'll be able to find several inns and bed and breakfasts around Main Street. Learn more about this charming small town in Massachusetts, and then pencil in a visit.
5. Stockbridge
Stockbridge, MA, USA
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Norman Rockwell found Stockbridge's Main Street so quaint and charming that he used it as inspiration for his painting "Stockbridge Main Street at Christmas." Take a walk through the village, stop for a coffee at one of the cafes, and pop into one of the galleries. You'll fall in love with the town just as Rockwell did. This is truly one of the best downtowns in Massachusetts, so start planning your next visit there.
6. Great Barrington
Great Barrington, MA, USA
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The Downtown Great Barrington Cultural District is home to several locally-owned businesses along with farm-to-table restaurants, entertainment venues, boutiques, and so much more! Take some time to stroll down Main Street to explore some of Great Barrington's most incredible offerings. Go ahead and start planning your visit to one of the best small towns in Massachusetts.
7. Amherst
Amherst, MA, USA
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You'll love the local shopping opportunities in downtown Amherst. With book and record shops, a vintage store, a bike shop, and an instrument shop among others, there's quite the eclectic mix of places to browse. There's also quite a bit of culture to experience at the museums, galleries, and cinema and you'll love the culinary options offered here as well. So plan a weekend trip here, or make it part of a fun road trip in Massachusetts.

These are the best downtowns in Massachusetts are truly the heart and soul of the state. Do you have a favorite downtown area? Tell us about it in the comments!

From small towns to hidden gems, Massachusetts is one of the best states to explore! Read about some of Massachusetts’s lesser-known attractions and then pay one a visit!

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More to Explore

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Jessica Bohl | September 15, 2022

What are some small rural towns in Massachusetts worth visiting?

Massachusetts has beautiful countryside, so it’s not surprise that there are many small rural towns that a worth a visit. Take Deerfield, for instance. This historic small town has a charming downtown area and plenty of museums and craft shops to explore. Be sure to visit in the fall when the trees glow with autumn colors. Montague is a small town in Western Massachusetts that is overflowing with rural charm. When you visit, check out the Montague Book Mill. This unique bookstore used to be a functioning mill but now is a cute café and used books shop.

What are some small towns in Massachusetts perfect for a weekend getaway?

If you want to escape the hustle and bustle of life, a quick weekend getaway to a charming small town in Massachusetts may be the perfect solution. Head over to the classic maritime town of Newburyport for a few days. Take in the busy waterfront, eat at some fantastic restaurants, and peruse the charming shops. Or, hop on a ferry and visit Edgartown on Martha’s Vineyard. This island town has fantastic shopping, amazing restaurants, and top notch accommodations. You won’t be disappointed!

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